HCl v HCLO

[Addallat]

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Why is HCl a stronger acid than HClO? Is it because the conjugate base of HClO isn't as great of a nucleophile?


Wouldn't the electron withdrawing effect of the chlorine in hypochlorite make it less reactive therefore the stronger acid?

 

[Addallat]

I have in my notes "a more stable conjugate base means a stronger acid"

does a more stable conjugate base mean a better nucleophile?

 

[texan2414]

I don't think so. Species that are stable are less reactive, so their nucleophilicity is probably not as high.

 

[Addallat]

So why is hypochlorite more reactive than hydrochloric acid? Wouldn't the electron withdrawing effect of the chlorine in hypochlorite make it less reactive therefore the stronger acid?

 

[kpandher]

I feel like the size and difference in electronegativity of HCl makes it a stronger acid.

 

[chemtopper]

I feel like the size and difference in electronegativity of HCl makes it a stronger acid.

In HClO --acidic H is bonded to Oxygen :H-O-Cl
However in HCl it is bonded to chlorine
H-Cl
Now if we compare the sizes of chlorine and oxygen - chlorine is bigger is size and hence taking away H+ from chlorine is more easy .The conjugate base Cl- is more stable because it can accommodate negative charge more nicely than OCl- where negative charge is on smaller oxygen atom .I agree that in OCl- electron withdrawing groups are also present but size is the dominating factor and we will decide the acidity of the compound on the basis of the size.

 

[Teleologist]

I have in my notes "a more stable conjugate base means a stronger acid"

does a more stable conjugate base mean a better nucleophile?

What do you mean by stability? How prone something is to protonation? Disproportionation? Reduction? Oxidation?

I don't think so. Species that are stable are less reactive, so their nucleophilicity is probably not as high.

Br- is a stable species in water solution, at least in the sense that it isn't likely to be protonated. But it's also a great nucleophile in water solution.